Sinteza novih derivata benzimidazola Sonogashira-inom reakcijom i njihova spektroskopska karakterizacija

master's thesis

• Title (english): Synthesis of benzimidazole derivatives using Sonogashira reaction and their spectroscopic characterization
• Author: Sanja Barić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Marijana Hranjec (član povjerenstva)
• Committee member: Šime Ukić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-07-12, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U ovom radu opisana je sinteza novih derivata benzaldehida i benzimidazola Sonogashira-inom reakcijom, njihova spektroskopska karakterizacija spektroskopijom NMR i UV/Vis te in silico analiza. Sonogashira-inom reakcijom p-klor i p-brombenzaldehida s odgovarajućim terminalnim alkinima uz Pd katalizator Pd(PPh3)4 i Pd2Cl2(PPh3)2 sintetizirani su p-alkinilni derivati benzaldehida 1-4 i 9-11. Reakcijom kondenzacije p-klor i p-brombenzaldehida s 2-(1H-benzo[d]imidazol-2-il)acetonitrilom pripravljeni su derivati benzimidazola 12 i 13 kojih su nadalje Sonogashira-inom reakcijom unakrsnog povezivanja prevedeni u alkinilne derivate benzimidazola 14-18. Reakcijom kondenzacije spojeva s hidroksimetilnim pobočnim lancem 21, 26 i 28 s 2-(1H-benzo[d]imidazol-2-il)acetonitrilom sintetizirani su derivati benzimidazola 23, 27 i 29. Sonogashira-inom reakcijom unakrsnog povezivanja spoja 29 s odgovarajućim terminalnim alkinima sintetizirani su spojevi 30 i 31. Strukturna i spektroskopska karakterizacija sintetiziranih spojeva provedena je 1H NMR i UV/Vis spektroskopijom, dok su biološka djelovanja i biološke mete predviđene in silico (PASS) analizom. In silico analiza spojeva ukazuje da spojevi s benzimidazolnom strukturom 12-18, 23-24, 27, 29-31 pokazuju vjerojatnost aktivnosti da djeluju kao snažni antineoplastici za široki spektar karcinoma.

Abstract (english)

This paper describes the synthesis of novel benzaldehyde and benzimidazole derivatives by Sonogashira cross-coupling reaction, their spectroscopic charactetization by NMR and UV/VIS spectroscopy and in silico analysis. Sonogashira cross-coupling reaction of p-chloro and p-bromobenzaldeyhe with appropriate terminal alkynes in the presence of Pd catalysts Pd(PPh3)4 and Pd2Cl2(PPh3)2 gave p-alkynyl benzaldehyde derivatives 1-4 and 9-11. Condensation reaction of p-chloro and p-bromobenzaldeyde with 2-(1H-benzo[d]imidazol-2-yl)acetonitrile gave benzimidazole derivatives 12 and 13, which were further converted into alkynyl benzimidazole derivatives 14-18 by Sonogashira cross-coupling reaction. Condensation reaction of compounds with hydroxymethyl side chain 21, 26 and 28 and 2-(1H-benzo[d]imidazol-2-yl)acetonitrile gave benzimidazole derivatives 23, 27 and 29. Sonogashira cross-coupling reaction of componud 29 with appropriate terminal alkynes gave compunds 30 and 31. Structural and spectroscopic characterization of novel compounds was carried out by 1H NMR and UV/Vis spectroscopy, while biological activity and biological targets were predicted by in silico analysis (PASS). In silico analysis showed that compounds with benzimidazole scaffold 12-18, 23-24, 27, 29-31 exhibit a powerful antineoplastic activity for a wide range of cancers.

• Keywords: benzaldehid; benzimidazol; akrilonitril; Sonogashira-ina reakcija
• Keywords (english): benzaldehyde; benzimidazole; acrilonitrile; Sonogashira cross-coupling reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:163881
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-06-02 12:16:01